Synthesis and characterization of oligoacenes for electronic applications
Final Report Abstract
Well-defined linear π-conjugated aromatic molecules play an important role in different fields ranging from supramolecular chemistry to electronics. Mainly, because of their precise chemical structure and conjugation, which gives rise to well-defined functional properties (low bandgap, high charge carrier mobility) and facilitate control over supramolecular organization. Polyaromatic hydrocarbons (PAHs) have emerged among the most promising candidates as organic semiconductors for the preparation of electronic devices. However there are multiple drawbacks in the preparation and manipulation of PAHs, due to their lack of stability and solubility. A good strategy to overcome this problem includes the lateral extension of the conjugation, which enhances the stability of PAHs. Such strategy together with the exchange of carbon atoms for heteroatoms and the introduction of large solubilising groups will be applied in order to prepare heteroacenes with enhanced stability and solubility. Through this project, we have developed a new approach for the synthesis of long and discrete PAHs to overcome all the above aspects related to their synthesis and solubility. This approach has provided oligomers a number of fused aromatic rings that oscillate between 19 and 22, exceeding the current methods for the synthesis of linear PAHs. In addition several optical, electrochemical and electric characterisation studies have demonstrated that such linear PAHs have a good potential in organic electronics in particular in NIR and transistor applications. This success has been achieved by overcoming all the problems related to the synthesis of the precursors and their solubility that have paved the way for the synthesis of larger PAHs.
Publications
- “Versatile 2,7-substituted pyrene synthons for the synthesis of pyrene-fused azaacenes” Org. Lett. 2012, 14, 4170-4173
S. More, R. Bhosale, S. Choudhary, A. Mateo-Alonso
(See online at https://doi.org/10.1021/ol301841h) - “11,11,12,12-Tetracyano-4,5- Pyrenoquinodimethanes (4,5-TCNP): Air-Stable Push-Pull ortho-Quinodimethanes with S2 Fluorescence”, Org. Lett. 2014, 16, 6096-6099
R. García, S. More, M. Melle-Franco, and A. Mateo-Alonso
(See online at https://doi.org/10.1021/ol5029332) - “Pyrene-fused pyrazaacenes: from small molecules to nanoribbons” Chem. Soc. Rev., 2014, 43, 6311-6324
A. Mateo-Alonso
(See online at https://doi.org/10.1039/c4cs00119b) - “Twisted Pyrene-fused Azaacenes” Chem. Comm., 2014, 50, 1976-1979
S. More, S. Choudhary, A. Higelin, I. Krossing, M. Melle-Franco and A. Mateo-Alonso
(See online at https://doi.org/10.1039/c3cc48742c) - "A short pyrene-fused pyrazaacene with red to near-infrared photoluminescence" Chem. Comm. 2015, 51, 8037-8040
R. Garcia, M. Melle-Franco and A. Mateo-Alonso
(See online at https://doi.org/10.1039/c5cc02459e) - “A Bis(triisopropylsilylethynyl)-Substituted Pyrene-Fused Tetraazaheptacene: Synthesis and Properties” Phys. Chem. Chem. Phys., 2016, 18, 11616-11619
A.B. Marco, C. Gozalvez, M. Olano, X. Sun, A. Atxabal, M. Melle-Franco, L.E. Hueso and A. Mateo-Alonso
(See online at https://doi.org/10.1039/c5cp07656k) - “K‐Conjugated Dibenzoazahexacenes” Org. Lett. 2016, 18, 4694-4697
Gabriella Antonicelli, Cristian Gozalvez, Ainhoa Atxabal, Manuel Melle-Franco, Luis E. Hueso, and Aurelio Mateo-Alonso
(See online at https://doi.org/10.1021/acs.orglett.6b02332) - “Synthesis of pyrene-fused pyrazaacenes on metal surfaces: towards one-dimensional conjugated nanostructures” ACS Nano, 2016, 10, 1033–1041
L. Jiang, A.C. Papageorgiou, S. Cheol; Ö. Sağlam, J. Reichert, D.A. Duncan, Y.-Q. Zhang, F. Klappenberger; S. More, R. Bhosale, A. Mateo-Alonso and J.V. Barth
(See online at https://doi.org/10.1021/acsnano.5b06340)
